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(3R,8R,9R,10R,13S,14S,17R)-17-acetyl-3-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,12,14,16-decahydrocyclopenta[a]phenanthrene-11,15-dione

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 6a6788ba-2eb1-473a-ace9-777021a01933
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
IUPAC Name (3R,8R,9R,10R,13S,14S,17R)-17-acetyl-3-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,12,14,16-decahydrocyclopenta[a]phenanthrene-11,15-dione
SMILES (Canonical) CC1C(C(C(C(O1)OC2CCC3(C4C(CC=C3C2)C5C(=O)CC(C5(CC4=O)C)(C(=O)C)O)C)O)OC)O
SMILES (Isomeric) C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@@H]2CC[C@@]3([C@H]4[C@@H](CC=C3C2)[C@@H]5C(=O)C[C@@]([C@]5(CC4=O)C)(C(=O)C)O)C)O)OC)O
InChI InChI=1S/C28H40O9/c1-13-22(32)24(35-5)23(33)25(36-13)37-16-8-9-26(3)15(10-16)6-7-17-20(26)18(30)11-27(4)21(17)19(31)12-28(27,34)14(2)29/h6,13,16-17,20-25,32-34H,7-12H2,1-5H3/t13-,16-,17-,20+,21-,22+,23-,24+,25-,26+,27+,28+/m1/s1
InChI Key MBDYRJBBFJLZNT-LHDDRJPHSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H40O9
Molecular Weight 520.60 g/mol
Exact Mass 520.26723285 g/mol
Topological Polar Surface Area (TPSA) 140.00 Ų
XlogP -0.30
Atomic LogP (AlogP) 1.49
H-Bond Acceptor 9
H-Bond Donor 3
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,8R,9R,10R,13S,14S,17R)-17-acetyl-3-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-17-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,12,14,16-decahydrocyclopenta[a]phenanthrene-11,15-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9677 96.77%
Caco-2 - 0.7430 74.30%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.7120 71.20%
OATP2B1 inhibitior - 0.7160 71.60%
OATP1B1 inhibitior + 0.8965 89.65%
OATP1B3 inhibitior + 0.9435 94.35%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.7053 70.53%
BSEP inhibitior + 0.7998 79.98%
P-glycoprotein inhibitior + 0.5785 57.85%
P-glycoprotein substrate + 0.5195 51.95%
CYP3A4 substrate + 0.7256 72.56%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8666 86.66%
CYP3A4 inhibition - 0.8320 83.20%
CYP2C9 inhibition - 0.9037 90.37%
CYP2C19 inhibition - 0.9405 94.05%
CYP2D6 inhibition - 0.9521 95.21%
CYP1A2 inhibition - 0.8440 84.40%
CYP2C8 inhibition + 0.5813 58.13%
CYP inhibitory promiscuity - 0.9598 95.98%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6212 62.12%
Eye corrosion - 0.9909 99.09%
Eye irritation - 0.9540 95.40%
Skin irritation + 0.5347 53.47%
Skin corrosion - 0.9228 92.28%
Ames mutagenesis - 0.7947 79.47%
Human Ether-a-go-go-Related Gene inhibition - 0.4826 48.26%
Micronuclear - 0.6700 67.00%
Hepatotoxicity - 0.6052 60.52%
skin sensitisation - 0.8639 86.39%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9778 97.78%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.5928 59.28%
Acute Oral Toxicity (c) I 0.3545 35.45%
Estrogen receptor binding + 0.6755 67.55%
Androgen receptor binding + 0.7306 73.06%
Thyroid receptor binding - 0.5423 54.23%
Glucocorticoid receptor binding + 0.6657 66.57%
Aromatase binding + 0.5947 59.47%
PPAR gamma - 0.5400 54.00%
Honey bee toxicity - 0.7169 71.69%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9574 95.74%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.62% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.57% 96.09%
CHEMBL253 P34972 Cannabinoid CB2 receptor 95.12% 97.25%
CHEMBL2581 P07339 Cathepsin D 93.49% 98.95%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.93% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 91.15% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 90.34% 91.07%
CHEMBL1994 P08235 Mineralocorticoid receptor 89.61% 100.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.62% 86.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.43% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.84% 95.56%
CHEMBL241 Q14432 Phosphodiesterase 3A 85.46% 92.94%
CHEMBL4303 P08238 Heat shock protein HSP 90-beta 85.41% 96.77%
CHEMBL5255 O00206 Toll-like receptor 4 85.10% 92.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.61% 99.23%
CHEMBL1937 Q92769 Histone deacetylase 2 82.15% 94.75%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.13% 95.89%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.00% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.93% 95.89%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Digitalis purpurea

Cross-Links

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PubChem 162922873
LOTUS LTS0034688
wikiData Q105160692